sex diaries

The Woman Flying to Vegas for a Second-Date Spanking

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Woman Flying to Vegas for a Second-Date Spanking: Female, 41, Boston, tour guide, heterosexual, single.


3:30 p.m. I’m at the beach, getting some sun before my trip to Vegas with the Dirty Gentleman in a few days. I send him a photo of my right breast falling out of my suit. I’ve been traveling these past few weeks and gotten into the habit of sending him such photos. My cell phone bill has gone through the roof.

5:10 p.m. Come home to find some things I ordered for the trip have arrived, just in time. I run upstairs to try on my new bra and nipple clamps and send a photo to the DG. He calls me his “shiny, glorious whore.” I only object to the possessive pronoun. I met the DG through friends, and we’ve only been on one date. Which, honestly, didn’t go very well. But we kept talking while I was on the road, and I found that I can open up about anything to him. One morning, after waking from a hot dream, I asked him how he would spank me if given the opportunity. His answer, “I’m pretty good with a belt,” got me so worked up that I immediately offered to fly out to meet him on his business trip. We’ve been raising the stakes ever since.

11:15 p.m. DG has an early flight tomorrow, so we should be good and go to sleep. And yet we’re chatting about the photo I sent him earlier. He tells me that his preference for naughty pictures is wet panties, then butt, then boobs. Last on his list, but most attention-grabbing, is “things in your p—y.” Apprehensively, I ask, “What kind of things? Are we talking things like your cock or things like a jar of peanut butter?” Thank God he’s talking reasonably sized phalluses, so I immediately grab a vibrator and oblige with a before and after shot. It’s odd how willing and eager I am to do whatever for this guy I barely know. Then, though he didn’t even ask for this, I send him a video of the vibrator at work. I’ve never done anything like this before, but somehow he’s just opened up my floodgates.

12:06 a.m. He leaves me hanging, but he tells me to call him when I’m ready to come so I can record it on his voicemail. I like it when he gets bossy with me.


6:40 p.m. The buildup of anticipation might be getting to us; we have a little fight. But he’s tired from travel and lack of sleep. And I’ve got most of my wardrobe spread out around my bedroom but still can’t decide what to pack. I shrug off the spat.

2:10 a.m. “I’m going to eat you as soon as you get to the hotel. You know that, right?” That’s what he thinks, but I have other plans. Don’t want to ruin the surprise though, so I stay mum.


9:15 p.m. My arrival is, understandably, awkward. I had planned to walk in, kiss him, then immediately drop to my knees and blow him. But I choked. Technically, this whole long weekend is only our second date, after one night at a bar and a bunch of calls and text messages. I do kiss him, though, and soon we’re on the bed. He tears my pants off and dives in. I like a man who keeps his promises.

10:30 p.m. I have the kind of orgasm that leaves you shaking and whimpering. I crawl up the bed away from him and curl up into a ball. He lies down next to me and kisses my shoulder; I swat him away. When I’m a live wire like this, I either need to be left alone to come down or smothered with all his body weight to feel anchored. There’s no middle ground.

10:50 p.m. I’ve got presents to open! A remote-controlled vibrator and a frighteningly large, shiny black dildo.

1 a.m. We’re wired and hungry. We dress and head out in search of food. I forgot my bra, so in the elevator, I rub up against his arm and he plays with my nipples through my T-shirt.

2:40 a.m. I’ve packed cute things to sleep in, but when I come to bed, he’s gotten naked, so I do the same. As I crawl into bed, he grabs my hips and starts licking my butt, then slaps it, hard. I want more, but even though the promise of a belting is what brought me out here, I’m not sure I’m ready for a spanking from this newish guy quite yet. Instead, I turn around and start blowing him. After a while, he tells me to stop toying with him and get serious about it. As soon as I do he comes, hard.


Around 5:00 a.m. His wake-up call isn’t until 6:15, but we’re half awake and reaching for each other. He starts my G-spot. Thank God we have the room at the end of the hall, because soon I’m pounding one hand against the headboard and biting the other one to keep from screaming. When I ask for more, he pushes his thumb into my butt. That’s not exactly what I expected, especially without lube; it takes a minute to settle in. I cry out. It may sound like showboating, but honestly I can’t help myself. I’m overwhelmed. It’s too much. I’m overstimulated and know that I won’t come, but we keep going until I’m whimpering and truly can’t take any more. He wraps himself around me and holds me tight until I stop shaking.

6:25 a.m. While he takes a shower, I text my friend to let her know that I’m alive and safe. Hey, you don’t run off across the country with a near stranger without leaving a trail of breadcrumbs. She asks why I’m awake so early, and I tell her about the thumb, though knowing her, she’s probably even more excited to hear that he licked me there last night.

7:30 a.m. DG heads out to have breakfast before work. I ask if he wants me to join him, but he’d rather be alone to get his head into work mode. Like a lazy kept woman, I go back to sleep.

4:40 p.m. Drinking a piña colada by the pool, I text the DG to tell him that my pussy is so sore that we may have to postpone our planned fisting attempt, then ask him when he’s coming “home” from work for our first full evening together. He wishes he could have stayed in bed with me this morning and asks me to wait to shower so we can do it together.

7:10 p.m. And that’s exactly what we do.

9:30 p.m. We meet up with a high-school friend of mine for dinner. Bringing a guy I barely know out to meet a friend I haven’t seen in years is already strange, but to make it even stranger, we’re acting all couple-y. He orders my meal, and I call him “sweetie.” Probably easier than explaining the real situation. I also find it much easier to play the doting girlfriend than to actually be one for serious. I hope I’m not leading him on.

12:45 a.m. In the casino, the DG is enthusiastically explaining craps to me, with all its obscure side bets and their implications, while the dealers smile and help him teach me. They seem to like us; they don’t mind that I’m taking up a space at the crowded rail even though I’m not betting. He kisses me whenever he wins big, and I make a few small bets with his winnings.

3:30 a.m. I guess we’ll sleep when we’re dead. As soon as I slip out of my dress, he’s got me pressed up against the window, taking me from behind as I look out over the Strip. I know no one can see us, but it’s still really hot feeling so exposed. He’s significantly taller than me, though, so although we try different positions, standing isn’t really working. He throws me down onto the bed instead.


6:15 a.m. The wake-up call rings. He says he’s getting up, so I don’t answer it. I sleep.

6:20 a.m. My alarm goes off. He says he’s up. I sleep.

8:54 a.m. Half-awake, I realize he’s spooned around me. I mutter, “Don’t you have to go to work today?” He looks at the clock and freaks.

9:08 a.m. He’s showered and out the door. Impressive! Still, I feel like I’m a bad influence or something.

9:30 a.m. Feeling terrible for not kicking him out of bed sooner, I putter around the room, hanging his suits, folding his clothes, and picking up his dirty laundry. Maybe I’m playing wifey, but I want to help out.

10:30 a.m. Back to sleep; I’m beat. I have no idea how he can function at work after two nights of this.

6:20 p.m. Damn him, he got back here before me and is already in the shower. We’re seeing a show at eight, and I don’t want to make him late. I join him. We bathe quickly, but then fall onto the bed afterwards instead of getting dressed. He fingers me, slowly adding more until he’s almost fisting me. But going past the knuckles hurts too much, and this is definitely not something we should be trying when we’re in a rush.

8:10 p.m. Late for the show, of course. It’s a Vegas revue, but there’s more bawdy humor than T & A. We snuggle but don’t get too worked up; the seats aren’t very conducive to playing along with the performers.

10:45 p.m. Over dinner, he’s talking a little too loudly about our attempt at anal the other night. I have to shush him but promise we’ll try again.

12:30 a.m. Back at the hotel, trying again. I suck him, then he puts me on all fours on the bed and goes to town. The thorough pounding he gives me is a nice return to the raunchiness we’d originally planned for this trip, after all the unexpected cuddling. He seems really grateful that I let him screw my butt as vigorously as he would my vag, and I wonder, How delicate are the women he’s been with before?


7:50 a.m. While he’s getting ready for work, I’m making a list of calls and e-mails I should get done today before I hit the pool. He adds two requests to my list: that I masturbate with the big black dildo and that I video it and send it to him while he’s working.

9:45 a.m. Hitting send. Seriously, all he has to do is ask.

7:30 p.m. He’s back at the hotel after his last day at work. We go out onto the balcony to take in the views. Curled up on the loveseat watching the sunset, I take off my top, then grab his hand and push it into my bikini bottom. No one can see us up on the 53rd floor!

8:15 p.m. There’s a leather bench in the hotel dressing room, surrounded by mirrors. I step out of my suit bottom and kneel on the bench, presenting my butt to him.

8:20 p.m. He’s gentle at first, but soon he’s smacking me really hard. Right when I think I can’t take any more, I hear him pull off his belt. Suddenly, I’m apprehensive, wondering what I’ve gotten myself into. There’s this combination of exhilaration and dread fighting it out in the pit of my stomach. I try to watch in the mirror, but he pushes my head down so I can’t see the lashes coming. After the heat generated from the spanking, the leather actually feels cool against me, and I begin to relax a bit. Then a sharp CRACK and I cry out, as much stunned as pained. This is like nothing I’ve ever felt before. Every time I think I need to stop, I get hit with a new wave of … pleasure? Endorphins? Stubborn determination to stick it out? He folds the belt doubled, and the lashes fall heavier, with more impact but less sting. I’m in a woozy daze. A few times I break position, and he pauses to give me a chance to use the safe word. But I never do.

9 p.m. I’m quivering and spent but giddy. He runs the bath, then comes back to take pictures so I can better see the marks he’s left.

9:10 p.m. We take a bath together in this huge soaking tub that looks out over the Bellagio fountains and deconstruct what just went down. He strokes my hair.

9:40 p.m. I had set an alarm so we’d get out of the tub with time to get ready for dinner. But we didn’t hear it, and now I’m frazzled and rushing. It’s really hard to do all the things we’d talked about as we planned this trip and still leave the bedroom on occasion. I wish we could stay another day.

10:25 p.m. Fancy dinner. He orders my cocktail, lights my cigarette. I’m not wearing underwear. He slips his hand under my skirt as we wait at the bar to be seated. This is such a lovely date.

1:10 a.m. We stop back at the room to drop off our leftovers before heading out dancing. But we ate and drank way too much and collapse onto the bed. I fall asleep, curled up against his chest.


Around 3 a.m. I wake and wash up for bed, change into a little silk nightgown. I’m determined to wear at least something cute that I packed. He’s awake. I try to go to sleep, but soon his hand moves up my thigh. He tells me he loves how wet I get. I love that he treats every physical reaction of mine like it’s a present for him. He starts to go down on me; I pull him down to me so he can indulge us both.

4:15 a.m. He hasn’t seen the dildo inside me in person, just in that photo I sent. I suggest that we use it for a DP of sorts while we’re having anal sex. We try, but it’s just too much for me.

5:30 a.m. We try to get a little sleep before checkout.

TOTALS: Five orgasms; two acts of masturbation; three acts of manual stimulation; three acts of cunnilingus; two acts of fellatio; one act of analingus received; one attempt and one successful act of anal sex; one attempt at DP; one almost fisting; one voicemail, two videos and multiple dirty pictures sent; two acts of exhibitionism; two acts of public fondling; two showers and one bath shared; one spanking with hand; and one spanking with belt.

The Woman Flying to Vegas for a Spanking